The Devil's dating dilemma (oneshot)
by vala411
Summary: A oneshot challenge between RedHawkdude, RedLegomaniac, Dragon1010, Thearizona and I. Date: May 28 2017. Prompt: I sold my soul to the devil a year ago. He gave it back to me today asking for a favor. Rules: 6000 word limit, the devil needs dating advice. Rated T for suggestive themes.


**A oneshot challenge between RedHawkdude, RedLegomaniac, Dragon1010, Thearizona and I**

 **Date: May 28 2017**

 **Prompt:** **I sold my soul to the devil a year ago. He gave it back to me today asking for a favor.**

 **Rules:** **6000 word limit, the devil needs dating advice**

 _ **Rated T for suggestive themes**_

* * *

 **The Devil's dating dilemma**

Hiccup let out a yawn before grumbling at something poking him as he rolled over and went back to sleep while shoving the thick blanket over his head and curling into a tight ball. There was a sigh of frustration before the blanket covering Hiccup was yanked away causing him to roll off of the bed with a yelp.

"What in hell!" Hiccup shouted as he stood up and looked around wildly.

"You're not in hell yet Hiccup." A voice said causing Hiccup to snap his head left. His eyes widened when he saw someone he never expected to see for a long time standing in his bedroom. The man wore a black suit and almost looked human if not for the red eyes he sported and the pitchfork he leaned on.

"What are you doing here?!" Hiccup asked shocked. "And why did you have to wake me up like that?"

"Hmmmm, not even a _Hello Lucifer, how's hell?_ " The man mumbled, not really looking bothered. "And for your information, I've been trying to rouse you for a while now. Honestly, even the dead aren't such heavy sleepers."

"What are you doing here?" Hiccup repeated. "It can't possibly be anything good."

"Why thank you for the compliment Hiccup." Lucifer smiled. "Unfortunately I've come here on a rather important matter."

"What does that have to do with me?" Hiccup asked stifling a yawn.

"So glad you asked Hiccup. First of all, we have this." Lucifer said while producing a scroll from a puff of smoke. "I'm sure you recognize it. After all you did sign it a year ago, selling your soul to me. I however see that things didn't go according to plan though."

"Like you wouldn't know." Hiccup mumbled as he glared at the man. "What conniving scheme are you up to now?"

"Oh Hiccup, really. You're making me blush from all the praise." Lucifer actually giggled. "However it was not my doing when she abandoned you. In fact today is your lucky day."

"It is?" Hiccup asked a little unsure.

"Why yes" Lucifer told him with a smile. "I am willing to return your soul to you, if you do me a favor."

Hiccup couldn't believe what he was hearing. "Alright what's the catch?"

"No catch Hiccup." Lucifer said. "You get your soul back if you agree to the favor."

Hiccup really wanted his soul back. He didn't actually regret selling it as he wanted to help someone. However what came after broke his heart. He studied Lucifer. There was no way he would hear what the favor entailed before he agreed it would see. "Alright fine. I'll do you a favor."

Lucifer smiled and the scroll containing the contract burned to ashes in front of Hiccup's eyes. "Alright, so I've retired."

Hiccup's eyebrows rose at that statement. "I didn't think the devil could retire."

"I've been at it for way too long." Lucifer sighed. "So my lovely daughter has taken over the title of Lord of Darkness and Hell."

"Alright" Hiccup said still shocked but hiding it well. He still didn't know what the favor was.

"Now there are some demon clans making a stink that my daughter needs to have an heir and they've offered up their sons as possible bachelors for her to choose from. This however poses a problem."

"I don't see it."

"Well if you must know Hiccup, I'm not one to get in the way of love, but if my daughter were to marry into one of the demon clans then they would attain the ruling power over Hell and my daughter would be dethroned. The demon clans still think of women as inferior. They're a bunch of power hungry leeches, not that I find anything wrong with that, but I'd rather enjoy my retirement with the succubuses' while not having to worry about my daughter."

"And that's where you come in." Lucifer smiled. "If my daughter were to fall for a human then she'll have no opposition from the clans vying for power."

"Wait you aren't asking me to marry your daughter are you?!" Hiccup shouted causing Lucifer to laugh.

"Oh Hell no Hiccup. You're too much of a goody goody for that." Lucifer laughed. "I'd probably have a heart attack if you became my son in-law."

"Eh…. thanks, I guess." Hiccup mumbled. "So what is it that you want me to do?"

"I was wondering if you'd be gracious enough host my darling daughter for her stay on Earth as well as help her navigate the dating scene. She's…. A bit rusty." Lucifer mumbled. "I believe the last time she was on Earth was during the Salem witch trials and last time she went on a date she ended up hurling several axes at a frog demon named Snotlout who asked her to have his children."

"Well given the circumstance, I'd probably would have done the same thing." Hiccup muttered.

"Well then, now that that has been cleared up, I'll leave her in your capable hands." Lucifer said as he smiled. "I'll let you get back to your sleep. She'll be here in the morning."

Hiccup nodded and then let out a yawn. He was too tired to care right now and flopped back on the bed after grabbing his blanket again. It wasn't long before Hiccup was sound asleep again.

He woke up early in the morning, whacking his alarm clock with much more force than was needed. Hiccup stifled a yawn and scratched his tousled auburn hair before getting out of bed and making his way to the kitchen. He needed coffee, copious amounts of coffee.

Hiccup however found, when exiting his bedroom, that he was not alone in his apartment. There was someone singing in his kitchen. At first he thought it was a thief but then he mentally slapped himself. 'Why would a thief be in his kitchen singing?'

He walked hesitantly to the kitchen door and opened it to reveal a petite blond woman flipping a pancake. She wore her hair in a single braid and smiled at Hiccup who was staring dumbfounded in the doorway. It was then that last night's conversation came back to him.

"I don't know if this is rude to ask but are you…"

"The Devil, Satan, Prince of darkness?" The woman said with a smile and then winked at Hiccup. "Sure I have all those titles but you can call me Astrid."

"Ironically that means Divine beauty." Hiccup mumbled causing Astrid to laugh.

"My dad can be weird at times." Astrid laughed.

"So, not to be rude but what are you doing?" Hiccup asked as Astrid proceeded to scoot him to a chair at the table.

"As you've agreed to help me out and let me stay here I've decided to surprise you with breakfast." She explained while setting a plate of hot pancakes, with a copious amount of syrup on top, in front of Hiccup along with a glass of orange juice.

"That's awfully kind of you." he told Astrid as she waited excitingly to see if he liked it. Hiccup not wanting to be insulting took a bite of the food. He immediately wished that he didn't as he struggled to swallow the piece of pancake. He couldn't feel his tastebuds anymore and he was sure that he was turning green.

"Astrid…..I…. eh…. Don't want to be rude but… I think this might be a biohazard." Hiccup mumbled when he finally could talk again and not be queasy.

"Oh Hiccup, you do know how to flatter a girl." Astrid giggled. "Dad says I have the devil's touch in the kitchen."

Honestly, Hiccup was rendered speechless. He just looked at Astrid and promised himself that he would be doing the cooking forever.

"Why don't I show you the guest room." Hiccup hastily said as he guided Astrid out of the kitchen. "I'll go freshen up and then we can work on the whole dating thing."

Hiccup got out of his pajamas and freshened up for the day after helping Astrid with her suitcases. He proceeded to wear a grey turtleneck and dark brown khakis. Hiccup took his laptop and sat on the couch in the living room. Astrid joined him not long after on the couch while looking at him curiously.

"So….. how would this dating thing go?"

"Well you could head out to bars and meet people. There are singles events or we could create a dating profile for you and see if anyone is interested." Hiccup explained as he showed Astrid a dating site.

"Meeting people at a bar seems tedious. I wish to meet as many possible suitors as I can."

"I guess we can go with online dating then. You can pick which men you like and ask them on a date to see if it will work." Hiccup told her. "First we'll need a profile picture."

"You wish for me to pose to get a man's attention?" Astrid asked quirking a brow.

"Yeah sure." Hiccup mumbled.

"I'll be back in a second!" Astrid told him before rushing to her room. Hiccup meanwhile got out his phone and clicked the camera app.

"Is this sexy enough Hiccup?" Astrid asked causing Hiccup to turn around and gape.

"OH MY FREAKING GODS!" Hiccup shouted as he quickly covered his eyes as a blush worked its way to his cheeks. Astrid was dressed in a royal purple chemise which was see through. "Astrid what are you wearing?!"

"You said, something to get a man's attention." Astrid explained as she walked towards Hiccup who still kept his hand in front of his eyes. "Wouldn't this give me the chance at the most suitors?" She asked and Hiccup could feel her warm breath near his ear. He shivered and then he heard Astrid whisper to him "It got your attention after all." Hiccup had to suppress a whimper as he had caught a glimpse of Astrid before covering his eyes.

"Astrid….. Could you please put on something… less revealing?" Hiccup pleaded, his cheeks still hot as he remembered Astrid so near him. She was indeed a very beautiful woman.

Hiccup heard a door shut and peeked through his fingers to see that Astrid had left the living room again. When Astrid came back out she was wearing a red mini dress. "Is this better?" She asked.

"Yes" Hiccup told her as he had her pose for a couple of pictures. Hiccup's blush had died down but he still glimpsed at Astrid when he thought she wasn't looking.

After choosing the best picture they decided to work on the profile.

Username: _Devilgirl19_

Occupation:

Age:

Height: _5'10"_

Religion: _I'll tell you later_

Drinks: _Sometimes_

Smokes: _Occasionally_

Body type: _Athletic_

Education:

Marital status: _Single_

Seeking: _Man ages 25-35_

Have kids: _No_

Want kids: _Yes, in a few years_

One liner: _Passionate, adventurous and quirky_

"So what do we put for the last three fields?" Hiccup asked Astrid.

"Well I do have a Master's degree." Astrid explained. "Demon University is quite advanced."

"You have an University?" Hiccup asked.

"Of course. We also have unions and conferences. We aren't barbarians." Astrid told him as she leaned against him while checking the profile. "As for occupation I suppose placing Ruler of Hell might be a turn off."

"Yeah…." Hiccup told her and then he had an idea. For occupation he filled in Supervising Manager. It was close enough. He looked at Astrid, she couldn't be older than him he thought and put 24 in the age category. Once the profile was done all that was left to do was wait.

Astrid was watching Hiccup curiously. "Hiccup why do you not have a girlfriend?"

She then noticed the pained look in his eyes and quickly said. "You…. You don't have to tell me if you don't want to."

"You might as well know." Hiccup sighed. "It's not really a secret."

"It isn't?" Astrid asked.

"No, you see I was married a year ago." He told her. "It's actually the reason I met your father."

"Did he ruin your wedding?!" Astrid asked worriedly. "If he did I would gladly punch him."

"No No. Nothing like that." Hiccup laughed. He really wanted to see Lucifer get punched one day. "It happened before the wedding. Amanda, my fiance, got into a car accident and the doctors said she wasn't going to make it. I loved her, I really did and I would have done anything for her."

"You met my dad then." Astrid now understood.

Hiccup nodded. "I sold my soul so that she could get better and it worked too. She made a miraculous recovery and we got married in spring."

"So… what happened? You said that you were married."

"Apparently I wasn't enough for her. She started sleeping with her yoga instructor and when I found out I asked her for a divorce. I don't think I've seen her sigh something so fast. Last I heard she moved in with him."

"Why that bitch! I might be a devil but that is just downright mean!" Astrid exclaimed. "I'll put her on my special list if you want?"

"It's alright Astrid." Hiccup tried to placate her. "She hurt me, I know, but I still would have done what I did to save her." He then mumbled. "I couldn't bare to see her in such pain." Astrid wasn't a devil for nothing. She sensed it but decided not to confront Hiccup about it yet.

"Hiccup you are too much of a goody two-shoes." Astrid mumbled. "I would have bitchslapped her to the Himalayas."

This caused Hiccup to laugh. "I might have wanted to get that on tape to be honest." It was then that Hiccup's computer chose to chime. They looked at the screen and saw that Astrid's profile had gotten some likes.

"Check these out. If you like any we can set up a date." He told her as Astrid flipped through the three profiles which had liked her page.

Astrid cringed as she saw one of the pictures. She however pointed to the other two. "I would like to meet these two." She told Hiccup as he showed her how to ask them if they'd be interested in meeting.

Once the dates were set she looked back at Hiccup and smiled. "Thank you!" She said and gave Hiccup a peck on the cheek. Astrid had a mischievous look in her eyes as she bent close and whispered into Hiccup's ear. "You know, I wouldn't mind if you wanted to get a closer look at my first choice of clothing. All you need to do is ask." She ran her hands down his sides, following his waist before tugging on his belt loops.

Hiccup's blush returned tenfold as he sputtered before turning to Astrid who was walking seductively back to her room. Hiccup turned his head back around as he noticed that he had been watching the sway of her hips. 'Temptress' ran through Hiccup's head. Another thought also joined in which caused Hiccup to let out a groan. 'You liked it.'

The day of the first date approached and in the meantime Astrid had lined up another couple of dates. She has been living with Hiccup for nearly a week now and enjoyed teasing him a bit. 'She liked his blush' she told herself as she looked in the mirror. She was dressed in a black cocktail dress with her hair done up. She grabbed her clutch purse as her date would be picking her up any moment. She bid goodbye to Hiccup who was placing a casserole in the oven. She still wondered why Hiccup wanted to do all the cooking.

Her date arrived and picked her up. He told her that they'd be going out to eat and Astrid expected to go to a restaurant. What she didn't expect was that they were going to eat at a fast food place. Astrid raised an eyebrow as they entered the establishment. She was definitely overdressed for the occasion. Her date meanwhile was glancing at an elderly woman. Astrid's eyebrows shot up when her date shouted "HI MOM!"

"What is your mother doing here?" She whispered to the man who gave her a weird look.

"Supervising our date." He simply told her and that's when Astrid ordered him to take her back home.

When she got back to Hiccup's apartment she bid Hiccup, who was watching reruns of Laverne and Shirley, good night before slamming the door to her room.

The second guy Astrid had lined up for a date wasn't any better in her opinion. He at least took her to a fancy restaurant but then in spiraled downwards. He proceeded to introduce her to the waiter as his fiance and soon to be wife and mother of his children all the while planning out their life together.

Astrid just gave the guy a look before standing up from the table and walking outside to hail a taxi. When she got back to Hiccup's apartment she proceeded to raid his liquor cabinet.

"So I'm guessing bad date?" Hiccup asked from the couch he was lounging on.

"This one will get a special place down there." She muttered before handing Hiccup a decanter filled with whiskey. She grabbed the glass bottle, placed it on the coffee table, and plopped down next to Hiccup. "Let's drink to being sensible." Astrid said as she clicked their glasses. Soon one drink turned into several, which turned into Astrid and Hiccup laughing at nothing in particular on the couch.

"Damn stupid rules of hell!" Astrid slurred. "I don't wanna choose a guy just to have kids!"

Hiccup merely hummed. He too was long past tipsy.

"I want a guy who likes me for me!" She mumbled and moved closer to Hiccup whose cheeks began to heat up. "Maybe someone I could have a bit of fun tying up." She smirked as she whispered that in his ear causing Hiccup to nearly choke on the sip of whiskey he just drank.

"A...Astrid" Hiccup sputtered as Astrid leaned in close, their lips barely touching.

"You don't have to lie to yourself anymore Hiccup. I already know." She whispered. "You still have feelings for your ex. I'm a devil, I can tell when someone is lying." She mumbled. "Want me to make you forget?"

It was then that Hiccup snapped out of the alcohol induced haze a bit. "I'm sorry Astrid, you're drunk. You don't know what you're saying." He whispered back as Astrid rested her head on his shoulder.

"You're nice Hiccup, I just want you to be happy. Is that weird for a devil to want?" She asked as Hiccup picked her up bridal style and carried her to her room, stumbling a bit.

"Such a gentleman" Astrid whispered as he tucked her in before closing the door.

The following morning greeted both of the apartment's occupants with headaches and hangovers. Both Hiccup and Astrid did remember the previous night and both blushed and tried to avoid eye contact. It got a little awkward in the coming weeks as both were too stubborn to talk about what had almost happened.

Hiccup sometimes stayed home, other times he would go to the movies with friends but Astrid never saw him go on dates. She on the other hand was still scheduling dates but many just ended disastrously.

One of her dates showed up two hours late and he was dressed in his work uniform which was a chicken mascot.

Another actually took her to church where he and the congregation proceeded to pray for her. OF ALL THE NERVE!

And then there was the one which had several outstanding warrants on him. He was arrested during their date and she was held for questioning.

And then there was they guy who said he preferred his women modest and quiet. Well she smirked remembering that one. Quite the scene she cause giving him a piece of her mind along with erectile dysfunction. Being the devil had it's perks after all.

There was also the whiner, the cryer, the gassy one, the psychopath, the groper. At some point Astrid wished she could give these guys a special place in hell.

Then there was one date who took a 30 minute business call at the restaurant table and was rude to the waitstaff. She just got up and walked to the ladies room where she called Hiccup to come pick her up. The car ride back to the apartment however was filled with silence as they didn't bring up what had happened before. Astrid was sure that she liked Hiccup more than a friend but she thought that her bringing up his ex wasn't such a good idea and now he might just dislike her.

Hiccup on the other hand knew he felt something for Astrid but he didn't want to get hurt again. His friends kept telling him that he should start dating again but every time he tried he would just think back to Amanda. He really did lie when he said she'd broken his heart. In fact she had shattered it, blaming him for their failing marriage as well as her need to cheat because he couldn't satisfy her enough.

Astrid and Hiccup entered the apartment and both went to their separate rooms. Astrid had been pacing for a while since she'd returned before she decided to throw caution to the wind. The giant pink elephant in the room had to be addressed. She decided then and there that she'd cancel the rest of her dates and focus on getting to know Hiccup better. Her dad did once tell her that somethings could be found right under your nose.

So now Astrid stood in front of Hiccup's door having donned the sexiest lingerie she had, which consisted of black lace panties and a bra before covering it with a short robe revealing her bare knees. She knocked on Hiccup's door and entered when she received an answer.

Meanwhile Hiccup couldn't sleep, and he simply lay on his bed staring at the dark ceiling. There was a knock on the door and Hiccup knew just who it was. He didn't know what to expect. Would he get laughed at, would he be put down again? Hiccup knew that Astrid wasn't that kind of woman and he secretly hoped that she liked him back but the insecurities were still there.

Astrid entered the room and Hiccup was grateful that the darkness hid the blush he was sporting when he saw Astrid in her loose fitting robe which clearly showed off the lingerie she was wearing.

"A….A...Astrid" He stuttered. "What can I do for you?"

"I think we need to talk." Astrid told him as she stepped into the room. The light from the hallway spilled through the open door as she walked towards Hiccup.

"A...About what?" Hiccup asked.

"Don't play dumb Hiccup, because I know you aren't." Astrid softly said as she got closer. "Let's be honest with each other. I like you. I've come to like you a lot these past few months that I've been staying here. What I want to know is how you feel."

"I've come to like you as well." Hiccup confessed causing Astrid to smile. "It's just….." He trailed off. "You deserve better." He murmured but Astrid still heard him.

"What makes you think you aren't just my type." Astrid whispered and gave his ear a playful nip as she circled her hands around his neck.

"I….. I…." Hiccup hesitated.

"There is doubt." Astrid mumbled as she gave him a kiss on the lips before pressing closer. She could feel that Hiccup was aroused yet he still held back. "Hiccup, throw away any doubt. I want you here and now! Or do I have to tie you up and have my wicked way with you." She smirked into his ear. Something in Hiccup snapped and he proceeded to pin Astrid to the wall and kiss her hard.

Their lovemaking lasted through the night and started again early in the morning. They clung to each other like starved lions. Astrid smiled as she twirled her finger in Hiccup's hair. He just grunted and pulled her closer while mumbling something about 'devils and to much stamina'.

From that night their relationship progressed steadily. Astrid took down her profile on the dating site and Hiccup became more outgoing, taking her on various dates and romantic outings. They were together for nearly five months already when someone unexpected dropped by on Hiccup's doorstep.

Hiccup raised his eyebrows when he opened the door to see his ex-wife standing there. She was dressed in a very short lavender skirt with a white blouse which had way too many buttons opened in Hiccup's opinion.

"Amanda, what are you doing here?" He asked as he tried to keep his face neutral.

"Why Hiccup darling I came to see you." Amanda said before she casually sauntered inside.

"I don't remember inviting you in." Hiccup muttered as he crossed his arms. "In fact I don't remember inviting you at all."

"Can't I just pop in to see my darling ex-husband?" She innocently asked which caused Hiccup to raise a brow.

"I thought you were too busy shaking up with… what was his name again? ….. Enrique?"

"Eric" Amanda corrected. "And no. He and I had a falling out."

Hiccup took a guess then. "He cheated on you." He deadpanned.

"With our pool boy." She muttered angrily.

"Well I wish him all the best then. Certainly better than a harpy like you."

"Oh come on Hiccup darling. I thought maybe we could put the past behind us and start again." She simpered but Hiccup didn't bat an eye.

"Oh but you see, I did put the past behind me." He told her and smirked. He saw her smile thinking she had won, that was until he said the next part. "You were quite a big part of that past. So glad I'm over it now."

Her smile faltered and she was going to say something again when Astrid came into the living room wearing very very revealing clothing while holding a pair of fuzzy red handcuffs.

"Hiccup honey! Are we going to have some fun or what?" She asked walking up to him and kissing him on the cheek while completely ignoring Amanda who was watching openmouthed.

"Excuse me! Just who the hell are you?" Amanda shrieked.

"Oh you must be Amanda." Astrid said while flicking a piece of imaginary lint from her shoulder. She then turned to Hiccup, ignoring Amanda again. "So is she leaving? Cause I want to try something new." She asked seductively causing Hiccup to grin.

"She was just on her way out." Hiccup stated.

"Now just hold on a minute!" AManda sputtered. "Just who is she?!"

"Fine…" Astrid shrugged. "I'm Astrid, Hiccup's future wife and Lord of the Underworld. Now if you excuse us…"

"THE WHAT?!" Amanda shouted.

"I'm The Devil bitch, Hiccup is mine so step off." Astrid calmly said as she conjured up a little fireball. "Maybe I should turn you crispy right now for getting into my cuddle time!"

That had Amanda running out of the door as if hell itself was on her heels. Hiccup lifted a brow at Astrid's antics before scooping her up and carrying her bridal style.

"So still want to try something?" She asked wiggling her brows suggestively while twirling the handcuffs.

"You are a minx." Hiccup laughed as he kicked open the bedroom door.

"And you love it." Astrid replied.

Somewhere on a beach in the Underworld Lucifer sat under an umbrella while being surrounded by a harem of women and sipping a glass of wine.

"Oh how I love retirement." He mumbled as he looked at the bloody sea before him. The women were all cuddling up to him when a waiter approached.

"Sir, you have a message." The waiter said as he handed him a tray with a letter on top. "It was sent with express demon mail."

Lucifer gingerly took the letter and smiled when he saw that it was from his darling daughter.

"Now what could Astrid be sending?" He asked himself as he opened the letter. Inside was a photograph of Astrid and surprisingly Hiccup. He turned over the photo and read the text there.

' _We are pleased to announce our engagement and upcoming nuptials_ ' The first line of text read. Lucifer quickly turned the picture back around and took a closer look at it. There he finally noticed the gleaming engagement ring his daughter was wearing.

Lucifer turned the picture over again and read the second line of text. It was written in a handwriting he didn't recognize. ' _So is it alright if I start calling you dad?_ ' was asked. Below that was written in his daughter's handwriting ' _Don't kill Hiccup_ '.

Right now killing Hiccup was farthest from his thoughts. Lucifer held a hand to his heart before he fainted, faceplanting into the sand.

Meanwhile on Earth, Hiccup was busy mashing potatoes when a chill ran up his spine. "I think your dad might have had that coronary." He mumbled causing Astrid to let out a bark of laughter.

"He'll get over it." She stated with a shrug as she tried to sneak a bit of the curry chicken Hiccup had made.

 **-The End-**


End file.
